You don't like the concept of relationships as "work," so why "hard" questions?
Whenever I read "relationships take work," I always thought, "Uh, no thanks." To me, that meant things like scheduling time for sex, "date nights," and pretending to be nice even when I wanted to shriek. Things that felt really fake.
With the Questions, the "work" of being truthful with each other was hard, but it certainly wasn't phony. It has given our relationship a very healthy edginess—not the kind that comes from jealousy and fights, but the kind that comes from trying to meet every circumstance with awareness and skillful honesty.
Well, except when we're just tired of trying and ignore each other. Sometimes we retreat to our corners. But the questions help us to reconnect, when we're ready.
When is the best time to ask these questions?
For some, a crisis may precipitate the conversation. For others, it may be a feeling of taking each other for granted, even a tiny bit. Anniversaries are a great time to reflect and take a pulse.
If you try to have this conversation too early, you'll know—the questions will sound silly. And there's no such thing as "too late," but the longer you let troublesome issues stew, the harder it will be. Wait until you both have the time and ability to focus. You may want to sit down at the kitchen table with a bottle of wine and run through every question. Or you can take one or two questions at a time, see how that goes.
Long drives, quiet walks, a dinner date, chilling on the couch (TV off)—all these are good settings. Answer only those questions that seem interesting or important to you. But note those that don't; perhaps they'll become relevant in the future.
Is it vital to reach agreement?
Absolutely not. You don't need a laundry list of perfectly synchronized answers. If you happen to agree, that's wonderful. If you don't, fine. Knowing your partner's thoughts and feelings is always good.